Portland’s mayoral primary had something to teach everyone about Rose City politics.

Fresh off his May 15 primary victory, mayoral candidate
Charlie Hales fired most of his staff last week. As a gesture of
appreciation, Hales handed each an autographed photo of himself posing
with the staffer he had just canned.

Meanwhile, Rep.
Jefferson Smith, the surprise second-place finisher, says he wanted
“healing” after a tough campaign. So his backers swarmed Twitter,
Facebook and blogs to pitch for the support of the candidate whose hopes
Smith had extinguished, Eileen Brady.

Voters may be sick of
the campaign just finished, but Smith and Hales are already working to
win in the November general election.

And no one has truly
answered the question that Portlanders are still asking: How did Brady—a
candidate who started with every advantage and spent a record $1.3
million in the primary—fail in such epic fashion?

Until the primary,
former City Commissioner Jim Francesconi, who spent nearly $1 million in
the 2004 mayoral primary, only to lose in the general election to a
former police chief, Tom Potter, was the high-water mark for political
folly.

The title now belongs
to Brady. She won just 22 percent, spending a jaw-dropping $46 per
vote—three times what her opponents spent per vote, and more than double
Francesconi’s historic $21.

Many of Brady’s
faults overshadowed Hales’ and Smith’s own shortcomings, and with her
gone, their weaknesses will stand in stark relief.

The way this race
played out has provided lessons for Smith, Hales and future city
candidates—but most important, lessons for voters as well.

Brady’s early polling showed an
unbeatable combination: a 50-year-old businesswoman with ties to a
beloved Portland institution, progressive cred and no connection to City
Hall. Her potential was “off the charts,” say two people familiar with
Brady’s early numbers.

There are struggles
in running for office that can be daunting even for someone with a
successful career, including establishing one’s identity with voters.
Brady sought to define herself as the sustainability candidate who could
bring jobs to Portland.

But Brady often
contradicted herself. While draping herself in green, she flip-flopped
on the proposed $3.5 billion Columbia River Crossing and adopted a
“build, baby, build” approach to win business and labor support.

She was also
unprepared for scrutiny. When her claim of being a co-founder of New
Seasons Market came into question, Brady attacked the news media for
questioning her; her son, Colin O’Brady, recently blogged that his
mother was the target of an “unfair and editorialized sexist negative
campaign.” (Brady didn’t return WW’s calls.)

When WW
reported that a police officer had excluded her from Tom McCall
Waterfront Park in 2003—and noted her threat to call “friends” at City
Hall to help her get out of the ticket—she responded by calling the cop a
liar. When her answers ran long during KATU’s debate, Brady on live TV
complained that the floor director (who stood in plain view) was making
it difficult for her to see when her time was up.

By contrast, Smith
and Hales took their knocks in stride. Smith dealt with public exposure
of his attention-deficit disorder, spoke frankly of the medication he
takes to manage it, and acknowledged a history of managerial mishaps
without getting defensive.

Hales faced
revelations that he’d avoided Oregon taxes as a Washington resident
while continuing to vote here—and at first didn’t tell the truth about
it. But he apologized (sort of) and addressed the issue directly (if
incompletely) at campaign events.

They also showed they
knew who they were and weren’t afraid to run on that image. When Smith
entered the mayoral race last September, he was five months late to the
party and, because of an injury, wore a patch over one eye. The two-term
state lawmaker—ostensibly the “Keep Portland Weird” candidate—promised
to run a “fun” campaign. He cracked jokes, turned cartwheels in the
street and tweeted madly.

As a former city
commissioner, Charlie Hales also had an identity: He’d championed the
streetcar, knew City Hall and promised steady (if slightly dull)
leadership as mayor, not unlike the campaign he ran. Hales’ persona was
as gray as his hair.

“I’m pretty
comfortable in my own skin,” Hales says. “I also, unlike others in
politics, have an actual life to go back to if voters disagree. This
gives me an even greater freedom to be myself than someone who might be
desperate for the next office.”

Know Thy Audience.

Brady oftentimes left events having won more votes for her opponents than for herself.

She was the guest of
honor at a dinner hosted last summer by two of Portland’s busiest
networkers, Stimson Lumber CEO Andrew Miller, the city’s largest
political contributor, and divorce lawyer Jody Stahancyk.

Neither Miller nor
Stahancyk would comment on the 20-person gathering, but others who
attended describe the evening as a debacle for Brady. Stephen Houze, a
leading criminal defense lawyer, and other guests pushed Brady without
success to describe the rationale for her candidacy.

Such scenes repeated
throughout the campaign. In private meetings, Brady (and her advisers)
told people she would be mayor and they needed to start dealing with
her.

Smith and Hales, with
more campaign experience, learned long ago to listen and respond. Hales
stuck to the script he knew from experience that voters wanted to hear:
He would return basics to City Hall. Smith knew his audience as
well—progressive Portland. He’d oppose the CRC and fight for equity.

Going forward,
however, both may encounter tension as they try to serve competing
interests—a challenge a mayor must face. While folksy, Hales’ campaign
took in more than $200,000 from development and real-estate interests,
and spoke of giving breaks in fees worth millions to business.

Smith has to reconcile his divided image as both the Occupy Portland candidate (as The American Prospect called him) and the choice of the Portland Police Association (which endorsed him and kicked in $10,000).

HALES: The candidate (left) risks getting painted as the new favorite of special interests.

Brady and Hales expected to run
against a weakened incumbent, Mayor Sam Adams. But Adams changed the
game in July by announcing he would not seek re-election.

Hales—traditionally
the proverbial tortoise in his campaigns—changed his message to fit the
new circumstances, but the recalibration was subtle. Smith jumped in
after Adams was out.

Brady never found a way to rebut Hales’ “experience” claim. Nor did she take Smith seriously—until it was too late.

“What she was saying
behind closed doors in terms of how real our candidacy was, I don’t
know,” Smith says. “But it was not Eileen but Charlie who told me I
didn’t have a chance.”

Smith and Hales are
already trying to define each other. Hales is calling for more results
and less rhetoric—a jab at his opponent, as Smith talks about an era of
new ideas—a poke at Hales’ being a retread.

Watch Thy Cash.

In his winning campaign, Hales
spent $798,000. Brady burned through nearly that much cash by April and
hadn’t yet bought a TV ad. Her campaign had big overhead costs, as if it
were a stimulus package for political consultants, yet ignored basic
media strategy, including cable TV and direct mail. She finished deeply
in debt after loaning herself $250,000.

Hales ended up loaning himself $100,000 while taking another $25,000 loan from a contributor.

Smith’s campaign
hoarded its limited cash, making DIY ads out of footage recycled from
campaign events. “I’m somewhat proud of being the only candidate to not
go six figures into debt,” Smith says.

But Smith and Hales
handled their early money well and kept pace with Brady in the most
important area: cash on hand. That’s what buys TV time, and Brady’s
spending allowed them to overtake her.

Know Thy City.

Portlanders see politics similarly
to artisanal meats—they want to know how the sausage is made. They want a
personal touch and know the difference between grass roots and
AstroTurf.

Smith had a head
start on his opponents in amassing and deploying an army of volunteers
to canvass the city. His focus on the “ground game” was bolstered by the
endorsement of key labor unions. Similarly, Hales, a veteran of
old-school retail politics, says, “I was on the doors for months and
months with no company.”

Brady took a different tack. She branded herself the big-money candidate by telling The Oregonian
in January she planned to raise $1 million for the primary. Her
endorsement by the Portland Business Alliance, the city’s most
influential business group, only reinforced that image.

Brady’s advisers
persuaded her to run for mayor as if she were running for the U.S.
Senate, saturating the broadcast media with ads. In contrast, Hales and
Smith counted hundreds of volunteers spread out across the city. Brady’s
couldn’t fill a bus.

It all ended in a sad scene on the afternoon of Election Day. Brady
sat at a table in Pioneer Courthouse Square for “office hours.” Two
supporters held a banner behind her, and a third aimed a campaign video
camera on Brady, who waited for voters to approach.

At first no one did, so Brady invited passersby to stop. Many had already voted. Others just weren’t interested.

Brady found a woman to stop and speak with her, and the candidate looked hopeful.

They talked for a long time, before the woman told Brady she wasn’t registered to vote.